I say do what you want, man. The thing about high school is, yeah, some people might say something behind your back, but no one's gonna be a total prick in front of everyone about it. That was cool back in middle school, but not so much now. Personally, I'm a ripped jeans guy, I just like the way it looks, but I dont drop $120 on Ezra Fitch whatever jeans. Hell, I really dont spend more than $30 on a pair of jeans, but thats besides the point. There was this dude a grade behind me who wore jean shorts and a white crew shirt everyday. Yeah, it did kind of look scrubby, but he was a cool cat, so no one cared.
My point is, do what you want to do and screw what everyone else says about it. Your opinion should always matter more to you and you should never go through life feeling like you should adhere to anyone elses's standards but your own. Dress to impress yourself, not others.